2,6-双(肼基)吡啶 | 23743-82-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2,6-双(肼基)吡啶
• 英文名称: 2,6-bis-hydrazinopyridine
• 英文别名: 2,6-Dihydrazinopyridine；(6-hydrazinylpyridin-2-yl)hydrazine
• CAS: 23743-82-0
• 化学式: C₅H₉N₅
• mdl: MFCD18384443
• 分子量: 139.16
• InChiKey: DLMNAUQCRQDOTG-UHFFFAOYSA-N

物化性质

• 熔点：
  125-127 °C (decomp)
• 沸点：
  354.5±52.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-双(肼基)吡啶 、 邻溴苯甲醛 在 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到2-N,6-N-bis[(2-bromophenyl)methylideneamino]pyridine-2,6-diamine
  参考文献：
  名称：

  由2,6-双-肼基吡啶合成2,6-双-吲唑-1-基吡啶的区域特异性

  摘要：

  研究了由2,6-双-肼基吡啶合成2,6-双-肼基吡啶和将这些双-基转化为2,6-双-吲哚-1-基吡啶。使用铁和铜介导的反应以及各种碱和配体系统地优化了双卤代芳基hydr向双吲唑的转化。通过改变溶剂，碱，过渡金属和配体，开发了向2,6-双-吲哚-1-基吡啶类配体的新的区域特异性途径。

  DOI：

  10.1016/j.tetlet.2011.07.081
• 作为产物：
  描述：

  2,6-二氟吡啶 在 肼 作用下， 反应 24.0h， 生成 2,6-双(肼基)吡啶
  参考文献：
  名称：

  2,6-双-肼基吡啶二水合物、其甲苯磺酸盐和2,6-双(3,5-二-叔丁基吡唑基)吡啶的晶体结构

  摘要：

  新化合物2,6-双-肼基吡啶二水合物(2)、其甲苯磺酸盐(3)和2,6-双-(3,5-二-叔丁基吡唑基)吡啶(4)的晶体结构如下获得单晶 X 射线衍射。2 的结晶发生在中心对称单斜空间群 P21/c (No. 14) 中，a = 9.6218(18), b = 6.7331(12), c = 13.489(3)；和 β = 109.292(8)∘ 和 Z = 4. 3 的结晶发生在中心对称单斜空间群 P21/c (No. 14) 中，a = 26.530(3), b = 16.6456(18), c = 9.9458( 10) 和 β = 96.828(5) 和 Z = 8，而 4 在 P21/n (No. 14) 中结晶，a = 15.0555(10), b = 10.4496(7), c = 16.9599(12) 和 β = 101.480(4) 和 Z = 4。这些是迄今为止报道的

  DOI：

  10.1007/s10870-005-5132-x

文献信息

• Synthesis and evaluation of analogues of HYNIC as bifunctional chelators for technetium
  作者：Levente K. Meszaros、Anica Dose、Stefano C. G. Biagini、Philip J. Blower

  DOI：10.1039/c0dt01608j

  日期：——

  6-Hydrazinonicotinic acid (HYNIC, 1) is a well-established bifunctional technetium-binding ligand often used to synthesise bioconjugates for radiolabelling with Tc-99m. It is capable of efficient capture of technetium at extremely low concentrations, but the structure of the labelled complexes is heterogeneous and incompletely understood. In particular, it is of interest to determine whether, at the no-carrier-added level, it acts in a chelating or non-chelating mode. Here we report two new isomers of HYNIC: 2-hydrazinonicotinic acid (2-HYNIC, 2), which (like 1) is capable of chelation through the mutually orthohydrazine and pyridine nitrogens and 4-hydrazinonicotinic acid (4-HYNIC, 3), which is not (due to the para-relationship of the hydrazine and pyridine nitrogens). LC–MS shows that the coordination chemistry of 2 with technetium closely parallels that of conventional 1, and no advantages of one over the other in terms of potential labelling efficiency or isomerism were discernable. Both 1 and 2 formed complexes with the loss of 5 protons from the ligand set, whether the co-ligand was tricine or EDDA. Ligand 3, however, failed to complex technetium except at very high ligand concentration: the marked contrast with 1 and 2 suggests that chelation, rather than nonchelating coordination, is a key feature of technetium coordination by HYNIC. Two further new HYNIC analogues, 2-chloro-6-hydrazinonicotinic acid (2-chloro-HYNIC, 4a) and 2,6-dihydrazinonicotinic acid (diHYNIC, 5) were also synthesised. The coordination chemistry of 4a with technetium was broadly parallel to that of 1 and 2 although it was a less efficient chelator, while 5 also behaved as an efficient chelator of technetium, but its coordination chemistry remains poorly defined and requires further investigation before it can sensibly be adopted for 99mTc-labelling. The new analogues 4a and 5 present an opportunity to develop trifunctional HYNIC analogues for more complex bioconjugate synthesis.

  6-氢肼基喹啉酸（HYNIC，1）是一种广泛使用的双功能钼结合配体，通常用于合成放射性标记的生物偶联物。它能够在极低浓度下有效捕获钼，但标记复合物的结构是异质的，尚未完全理解。尤其值得关注的是，在无载体加入水平下，它是以螯合或非螯合模式起作用。我们在此报告了两种HYNIC的新异构体：2-氢肼基喹啉酸（2-HYNIC，2），它（如1一样）能够通过相互邻位的氢肼和吡啶氮实现螯合，以及4-氢肼基喹啉酸（4-HYNIC，3），由于氢肼和吡啶氮的对位关系，它无法螯合。LC–MS显示，2与钼的配位化学与传统的1非常相似，在潜在标记效率或异构体方面没有显著优劣之分。无论共配体是三氨基乙酸还是EDDA，1和2都形成了失去5个质子的复合物。然而，配体3仅在非常高的配体浓度下才会与钼形成配合物，这与1和2形成了明显对比，表明螯合而非非螯合配位是HYNIC与钼配位的关键特征。此外，还合成了另外两种新的HYNIC类似物：2-氯-6-氢肼基喹啉酸（2-氯-HYNIC，4a）和2,6-二氢肼基喹啉酸（diHYNIC，5）。4a与钼的配位化学与1和2基本相似，尽管它的螯合效率较低，而5也表现出作为钼的高效螯合剂，但其配位化学尚未明确，需要进一步研究，以便可以合理地应用于99mTc标记。新的类似物4a和5为开发三功能HYNIC类似物以合成更复杂的生物偶联物提供了机会。
• [EN] MOLECULAR PLATFORMS HAVING TRANSITION METAL GRID COMPLEXES FOR A BINARY INFORMATION RECORDING MEDIUM<br/>[FR] PLATES-FORMES MOLECULAIRES COMPRENANT DES COMPLEXES DE GRILLES DE METAUX DE TRANSITION POUR UN SUPPORT D'ENREGISTREMENT D'INFORMATIONS BINAIRES
  申请人：THOMPSON LAURENCE K

  公开号：WO2005116039A1

  公开（公告）日：2005-12-08

  The present invention provides a novel class of molecular coordination compounds, and more particularly, square supramolecular metal coordination grids of the formula (I): [Ma2(L)2a]Xz (I), wherein M is a transition metal: a is 3, 4, 5 or 6; X is a counterion; z is 2 to 60 and L is as defined in the application. The present invention also provides the use of the square supramolecular metal coordination grids in a binary information recording medium, and a method of forming such a binary information recording medium.

  本发明提供了一类新型的分子配位化合物，更具体地说，提供了符号为(I)的正方形超分子金属配位网格：[Ma2(L)2a]Xz (I)，其中M是过渡金属；a为3、4、5或6；X是一个反离子；z为2至60；L如申请中所定义。本发明还提供了将这些正方形超分子金属配位网格用于二进制信息记录介质的用途，以及形成这样的二进制信息记录介质的方法。
• Electronic effects in the reaction of 1,3-diaryl-1,3-diketones with hydrazinopyridines
  作者：Nathan C. Duncan、Charles M. Garner、Tim Nguyen、Fernando Hung、Kevin Klausmeyer

  DOI：10.1016/j.tetlet.2008.07.104

  日期：2008.9

  The regioselectivity of the condensation of electronically unsymmetrical 1,3-diaryl- 1,3-diketones with 2-hydrazinopyridine and 2,6-bis-hydrazinopyridine to form N-(2-pyridyl)-3,5-diarylpyrazoles was studied. Significant electronic effects on regioselectivities were observed, and regioselectivities were opposite to those exhibited by perfluoroalkyl/alkyl 1,3-diketones. The electronic effects correlate well to the difference between the Hammett sigma(+) coefficients of the para substituents on the aryl rings. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and characterization of 2,6-bis-hydrazinopyridine, and its conversion to 2,6-bis-pyrazolylpyridines
  作者：Kimberly A. Brien、Charles M. Garner、Kevin G. Pinney

  DOI：10.1016/j.tet.2006.01.086

  日期：2006.4

  2,6-Bis-hydrazinopyridine has been prepared and characterized for the first time. This material is useful for the preparation of a wide variety of 2,6-bis-pyrazolylpyridines. This approach represents the most efficient preparation to date of sterically crowded 2,6-bispyrazolylpyridines, and the only method for the preparation of pyrazolylpyridines containing unsymmetrically 3',5'-disubstituted pyrazoles with the larger groups in the 5' positions. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis and structural characterization of 2,6-bis(1,2,4-diazaphospholyl-1-yl)pyridine zinc and 2,6-bis(1,2,4-diazaphospholyl-1-yl)pyrazine copper complexes
  作者：Minggang Zhao、Pangpang Li、Xiaodong Xie、Jihu Su、Wenjun Zheng

  DOI：10.1016/j.poly.2014.07.040

  日期：2015.1

  Several novel derivatives of mono- and bis(1,2,4-diazaphosphol-1-yl)pyridine (or pyrazine) as well as the first 2,6-bis(1,2,4-diazaphosphol-1-yl)pyridine (bdppy) and 2,6-bis(1,2,4-diazaphosphol-1-yl)pyrazine (bdppz) metal complexes [Zn(bdppy)2](2+)center dot.2ClO(4)(-) and [bdppz)Cu(NCMe)](2+)center dot 2ClO(4)(-) were prepared and structurally characterized. The complex [Zn(bdppy)(2)](2+)center dot.2ClO(4)(-) has a higher local concentration of low-valent phosphorus (sigma(2)lambda(3)) on the periphery of the molecule. All the compounds were characterized using H-1, C-13H-1}, P-31H-1} NMR and IR spectroscopy, and X-ray crystallography. The properties of the compound [(bdppz)Cu(NCMe)](2+)center dot 2ClO(4)(-) were studied using EPR spectroscopy and magnetic susceptibility measurements. (C) 2014 Elsevier Ltd. All rights reserved.